Curable compositions, reaction products of which are reworkable through thermal decomposition, are provided. Specific compounds useful in such curable compositions, as well as curable compositions and thermosets incorporating such compounds, are provided in the present invention. The compounds include a cyclic hydrocarbon moiety including an oxirane or thiirane group and an aromatic ether moiety including an oxirane or thiirane group. The cyclic hydrocarbon moiety and the aromatic ether moiety are joined to each other through an oxycarbonyl-containing linkage or a thiocarbonyl-containing linkage, preferably a secondary or tertiary linkage. Compositions incorporating such compounds are capable of curing by exposure to a specific temperature, and are decomposable at a temperature in excess of the curing temperature, thus providing a composition which is reworkable.
Legal claims defining the scope of protection, as filed with the USPTO.
1. A curable composition, reaction products of which are reworkable through thermal decomposition under exposure to temperature conditions in excess of those used to cure the composition, said curable composition comprising a compound containing a cyclic hydrocarbon moiety including an oxirane or thiirane group and an aromatic ether moiety including an oxirane or thiirane group, said cyclic hydrocarbon moiety and said aromatic ether moiety being joined to each other through an oxycarbonyl-containing linkage or a thiocarbonyl-containing linkage.
2. A curable composition as in claim 1 , wherein said cyclic hydrocarbon moiety including an oxirane or thiirane group is a cycloaliphatic epoxy or episulfide, respectively, moiety.
3. A curable composition as in claim 1 , wherein said aromatic ether moiety including an oxirane or thiirane group is an aromatic glycidyl or thioglycidyl ether, respectively, moiety.
4. A curable composition as in claim 1 , wherein said compound is represented by the formula: where R is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; each R 1 is independently selected from hydrogen, methyl, ethyl, propyl, and isopropyl; R 2 and R 3 are independently selected from hydrogen, methyl, ethyl, propyl, phenyl, tolyl, and benzyl; R 4 is independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; p is an integer from 0-4; and X and Y are independently selected from O and S.
5. A curable composition as in claim 4 , wherein said compound is selected from the group consisting of:
6. A thermosetting resin composition, reaction products of which are capable of softening and losing their adhesiveness under exposure to temperature conditions in excess of those used to cure the composition, said composition comprising: (a) a curable resin component, at least a portion of which comprises a compound containing a cyclic hydrocarbon moiety including an epoxy or episulfide group and an aromatic ether moiety including an epoxy or episulfide group, said cyclic hydrocarbon moiety and said aromatic ether moiety being joined to each other through an oxycarbonyl-containing linkage or a thiocarbonyl-containing linkage; (b) optionally, an inorganic filler component; and (c) a curing agent component comprising a member selected from the group consisting of anhydride compounds, amine compounds, amide compounds, imidazole compounds, and combinations thereof.
7. A thermosetting resin composition as in claim 6 , wherein said cyclic hydrocarbon moiety including an epoxy or episulfide group is a cycloaliphatic epoxy or episulfide, respectively, moiety.
8. A thermosetting resin composition as in claim 6 , wherein said aromatic ether moiety including an epoxy or episulfide group is an aromatic glycidyl or thioglycidyl ether, respectively, moiety.
9. A thermosetting resin composition as in claim 6 , wherein said compound is represented by the formula: where R is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; each R 1 is independently selected from hydrogen, methyl, ethyl, propyl, and isopropyl; R 2 and R 3 are independently selected from hydrogen, methyl, ethyl, propyl, phenyl, tolyl, and benzyl; R 4 is independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; p is an integer from 0-4; and X and Y are independently selected from O and S.
10. A thermosetting resin composition as in claim 9 , wherein said compound is selected from the group consisting of:
11. A thermosetting resin composition as in claim 6 , wherein said curable resin component further comprises cycloaliphatic epoxy compounds, aromatic glycidyl ether compounds, and mixtures thereof.
12. The composition according to claim 6 , further comprising a flowability agent.
13. The composition according to claim 12 , wherein the flowability agent is a member selected from the group consisting of silanes, titanates, and combinations thereof.
14. The composition according to claim 6 , further comprising an adhesion promoter.
15. The composition according to claim 14 , wherein the adhesion promoter is a member selected from the group consisting of glycidyl trimethoxysilane, gamma-amino propyl triethoxysilane, and combinations thereof.
16. The composition according to claim 6 , further comprising a cyanate ester.
17. The composition according to claim 6 , wherein the inorganic filler component may be selected from the group consisting of materials constructed of or containing reinforcing silicas, aluminum oxide, silicon nitride, aluminum nitride, silica-coated aluminum nitride, boron nitride, and combinations thereof.
18. The composition according to claim 6 , wherein the anhydride compounds of the curing agent component may be selected from the group consisting of hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, 5-(2,5-dioxotetrahydrol)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, and combinations thereof.
19. The composition according to claim 6 , wherein the amine compounds of the curing agent component may be selected from the group consisting of dicyandiamide, diethylenetriamine, triethylenetetramine, diethylaminopropylariine, m-xylenediamine, diaminodiphenylamine, isophoronediamine, menthenediamine, polyamides, 4,4 -methylenedianiline, 4,4 -methylenebis(cyclohexylamine), and combinations thereof.
20. The composition according to claim 6 , wherein the amide compounds of the curing agent component may be selected from the group consisting of dicyandiamide and combinations thereof.
21. The composition according to claim 6 , wherein the imidazole compounds of the curing agent component may be selected from the group consisting of imidazole, isoimidazole, 2-methyl imidazole, 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methylimidazole, 2-methylimidazole, 2-undecenylimidazole, 1-vinyl-2-methylimidazole, 2-n-heptadecylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl 4-methylimidazole, 1-benzyl-2-methylimidazole, 1-propyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-guanaminoethyl-2-methylimidazole, addition products of an imidazole and trimellitic acid, addition products of an imidazole and 2-n-heptadecyl-4-methylimidazole, phenylimidazole, benzylimidazole, 2-methyl-4,5-diphenylimidazole, 2,3,5-triphenylimidazole, 2-styrylimidazole, 1-(dodecyl benzyl)-2-methylimidazole, 2-(2-hydroxyl-4-t-butylphenyl)-4,5-diphenylimidazole, 2-(2-methoxyphenyl)-4,5-diphenylimidazole,2-(3-hydroxyphenyl)-4-,5-diphenylimidazole, 2-(p-dimethylaminophenyl)-4,5-diphenylimidazole, 2-(2-hydroxyphenyl)-4,5-diphenylimidazole, di(4,5-diphenyl-2-imidazole)-benzene-1,4,2-napnthyl-4,5-diphenylimidazole, 1-benzyl-2-methylimidazole, 2-p-methoxystyrylimidazole, and combinations thereof.
22. The composition according to claim 6 , wherein the curing agent component is used in an amount of from about 3 to about 60 parts by weight, per 100 parts by weight of the curable resin.
23. The composition according to claim 12 , wherein the flowability agent is selected from octyl trimethoxy silane, methacryloxy propyl trimethoxy silane, titanium IV tetrakis 2,2-bis (2-propenyloxy)methyl -1-butanolato-0 bis(ditridecylphosphito-0), dihydrogen 2 , and combinations thereof.
24. The composition according to claim 6 , wherein said composition is capable of sealing underfilling between a semiconductor device including a semiconductor chip mounted on a carrier substrate and a circuit board to which said semiconductor device is electrically connected.
25. A compound represented by the formula: where R is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; each R 1 is independently selected from hydrogen, methyl, ethyl, propyl, and isopropyl; R 2 and R 3 are independently selected from hydrogen, methyl, ethyl, propyl, phenyl, tolyl, and benzyl; R 4 is independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4 alkoxy, halogen, cyano, nitro and phenyl; p is an integer from 0-4; and X and Y are independently selected from O and S.
26. A compound as in claim 25 , wherein said compound is selected from the group consisting of:
Cooperative Patent Classification codes for this invention. Click any code to explore related patents in that topic.
September 5, 2000
September 30, 2003
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